Lithium hydroxide, monohydrate → 4-((3-Fluoro-4-(5-(1-phenylcyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)phenyl)amino)-4-oxobutanoic acid

HRID 1177635Notes

Reaction equation

HRID 1177635 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:26][C:27](=[O:34])[CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.C1COCC1.O.O.[OH-].[Li+]>>[F:1][C:2]1[CH:3]=[C:4]([NH:26][C:27](=[O:34])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:18][CH2:19]1)[N:11]=2

Participants

4

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 67111772Methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenylamino)-4-oxobutanoate

Product 1

HCID 573943294-((3-Fluoro-4-(5-(1-phenylcyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)phenyl)amino)-4-oxobutanoic acid

Procedure

To methyl 4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-phenylamino)-4-oxobutanoate (123 mg, 0.259 mmol) was added THF/water (4:1) (2.587 m, 0.259 mmol) and lithium hydroxide hydrate (33 mg, 0.776 mmol) before it was stirred at ambient T for 30 min. The reaction mixture was concentrated, triturated with water, filtered, washed with water, and dried in a vacuum oven to give the title compound. MS (ESI) m/z: Calculated: 461.1; Observed: 462.0 (M++1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with water
  3. filtrationfiltered
  4. washwashed with water
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-31e8abd97bf249af9d78b12cc7017df2
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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